Hydrochloric Acid → 3-Chloro-5-(3-fluorosulfonylphenylazo)-2-hydroxybenzaldehyde oxime

HRID 263152Notes

Reaction equation

HRID 263152 reaction equation
[Cl:1][C:2]1[C:3]([OH:22])=[C:4]([CH:7]=[C:8]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([F:21])(=[O:20])=[O:19])[CH:13]=2)[CH:9]=1)[CH:5]=O.Cl.[NH2:24][OH:25].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[C:3]([OH:22])=[C:4]([CH:7]=[C:8]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([F:21])(=[O:20])=[O:19])[CH:13]=2)[CH:9]=1)[CH:5]=[N:24][OH:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 1356774423-Chloro-5-(3-fluorosulfonylphenylazo)-2-hydroxy benzaldehyde

Product 1

HCID 1363987993-Chloro-5-(3-fluorosulfonylphenylazo)-2-hydroxybenzaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-5-(3-fluorosulfonylphenylazo)-2-hydroxy-benzaldehyde (23.8 g, 0.07 mol) was added to 250 ml ethanol, followed by hyroxylamine hydrochloride (5.04 g, 0.072 mol) and sodium hydroxide (2.88 g, 0.072 mol). The reaction was brought to reflux for 30 minutes and then cooled to room temperature. The mixture was then poured into ice and hydrochloric acid, resulting in the formation of a precipitate which was filtered off, washed with water, and dried in a vacuum oven (55° C.). The yield was 22.5 g (90%).

Workup

  1. temperatureto reflux for 30 minutes
  2. customresulting in the formation of a precipitate which
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried in a vacuum oven (55° C.)

Sources & evidence

ORD record
ord-01923fdcfdd64eb28c5da51d4afcecf2
Source dataset
uspto-grants-1979_05
Patent number
US04156609

Reaction notes

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